


Dean?

by kuza



Category: Supernatural
Genre: Anal Fingering, Anal Fisting, Anal Gaping, Anal Play, Come Eating, Come Swallowing, Destiel - Freeform, Dom/sub, Dominant Castiel, First Time, Fisting, Gay, Hand Jobs, M/M, Masturbation, Oral Sex, Orgasm, Panty Kink, Role Reversal, Smut, Submissive Dean
Language: English
Status: Completed
Published: 2019-05-25
Updated: 2019-05-25
Packaged: 2020-03-17 04:46:23
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,153
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18958162
Author URL: https://archiveofourown.org/users/kuza/pseuds/kuza
Summary: As much as Castiel loves dominating his little boy, he couldn't help but wonder what it would feel like to have Dean's fist inside of him. He's nervous to ask but glad when he finally does.





	Dean?

**Author's Note:**

> My first ever Supernatural fic! This is also my first fic in a long, long time. Excuse me if there are any errors (I doubt it because my bestest friend beta'd for me). Enjoy!

“What’s going on Cas?” Dean frowned as he looked at his lover. They’d been snuggling and kissing for a while now, which for the two of them usually ended up in sex. However this time Cas seemed to be… holding back a little bit. 

“Cas?” Dean pouted when his angel boyfriend didn’t reply, what was the matter with him?

“I- it’s- it’s nothing Dean.” Castiel tried to reassure the younger man. 

“Cas, I love you,” Dean said, looking his boyfriend right in the eyes.

“I know,” Castiel nodded. “I love you too.”

“Then tell me what’s going on in that head of yours, I’m no angel, I’m no mind reader. You have to talk to me, Cas,” Dean said as he sat up a bit more straight on the couch. Was it something he had done or said? Maybe he had pissed Castiel off without realizing. 

“You- you know when, when we sometimes do… stuff,” Castiel started and he could feel his cheeks turn red. It wasn’t like him, the dominant one in the relationship, to act like this. But there was something on his mind, it had been for days, he needed to know.

“Stuff,” Dean nodded and then instantly shook his head. “You’ve got to give me a little bit more than that, Cas.”

“When I erm-” the angel frowned as he balled his fist, “when I fist you.”

“Yeah I know about that,” the younger man said and a cheeky smile appeared on his face. Was that what his lover was acting all anxious about? “You want to fist me, babe?”

“No,” Castiel shook his head but instantly felt regret for the sad pout he’d put on his boyfriend’s face. “I mean yes, I- I always want to do that, Dean but-”

“But what, Cas?” Dean was getting a little impatient, what the hell was he getting at?

“I- I want you to- to do that to me,” Castiel said as he bit his lip. Could he even ask this of his submissive boyfriend? Was it appropriate of him to ask such a thing from Dean?

“You- you want me to fist you?” Dean’s eyes widened. Never in a million years did he think he’d hear that from the angel. 

“Unless you don’t want to, Dean then that’s fine too I mean-”

“No it’s fine,” Dean smiled as he reached for Castiel’s hands, holding them both in his own. “I’m just a little surprised you asked is all.”

“I am too, but you always seem to enjoy it so much, Dean it- it made me curious,” Castiel admitted as he squeezed his lover’s hands.

“I can do that for you,” Dean nodded as he felt excitement rush through his body. He was the bottom in this relationship, he usually took Castiel’s fist, but he was willing to do this for his lover, it was something new for them to try. He wondered how Cas would take it, considering Dean had only ever had a finger or two up there when he sucked Castiel off. 

“Can- can I ask for one more thing?” Castiel then asked, looking at his beautiful boyfriend.

“Sure,” Dean nodded.

“Will you wear your pretty pink panties while you do so?” Castiel bit his lip, he loved seeing his boy in his favorite lingerie.

“Of course,” Dean grinned as he started to get up from the couch. “Let me get changed and I’ll be right back,” he winked at the angel. “Don’t you change your mind now.”

“Oh I won’t,” Castiel smiled back at the younger man as he finally felt himself relax, Dean had agreed to what he wanted to try and he couldn’t be more excited. 

Dean couldn’t help the smile on his face as he rushed into their bedroom and got rid of his clothes as quickly as he could. ‘Pretty pink panties’, Castiel had said, except Dean had multiple pairs that could be considered to be pretty pink ones. He settled for his own personal fave though, yes, those would do. He stepped into them and quickly pulled the fabric up over his thighs until it was tight around his bottom. He admired himself in the mirror for a brief moment, grinning at how tight it was wrapped around his butt. Dean made sure to grab their favorite lube for this ‘special’ activity and then he walked back into the living room. 

“Cas!” Dean laughed as the angel was already naked, his cock hard against his stomach and his cheeks flushed red.

“I- I couldn’t help myself, Dean,” Castiel admitted as he admired his lover, now in pretty pink underwear. 

“That’s alright, I get it. That’s how I feel whenever you come up with a new idea,” the younger man nodded as he walked over to the couch, getting between the angel’s legs and onto his knees. “Think this will work best, that’s how you tend to do it.”

Castiel smiled and nodded, proud of his boy. Turns out Dean actually picked up some things as well whenever he’s getting his brains fucked out. 

“Cas?”

“Yeah?”

“If this at any point becomes too much or I’m hurting you whatsoever, you have to let me know, okay?” Dean asked as he gently rubbed up and down the angel’s thigh. 

“I will,” Castiel nodded. He trusted Dean, he knew the younger man wouldn’t hurt him, at least not on purpose. Oh no, Dean would probably take his sweet time just like Castiel always did on him. 

“Because this is quite something different than just two fingers,” Dean blushed a little as he said that, he could barely wrap his head around the fact that he got to do this to his Dom. 

“I know,” the angel said as he leaned forward, running a hand through Dean’s hair before tugging on it, pulling Dean up and over his own body and pressing their lips together. “I trust you,” Castiel said as he pulled back and let go of Dean’s hair. 

That was apparently all that Dean needed to hear, as he smiled widely and got back onto his knees. “Well, you’ll have to put your feet on the edge of the couch here and here,” Dean said as he pointed to where he would have his own feet were the situation reversed. 

“Mhm, I can do that,” Castiel nodded as he followed his lover’s directions. 

Even though you’d think this situation would just be the opposite of what they normally did, it was still different. If it were Castiel giving Dean a good fisting he wouldn’t just direct his lover where to put his feet, no. Castiel would make sure to place those feet exactly where he wanted them himself. 

“Alright,” Dean nodded as he grabbed the bottle of lube, flicking open the cap and squeezing some onto his fingers as well as a slight bit onto Castiel’s bright pink hole. 

The angel shuddered a bit as the cold lube touched his sensitive skin, it felt a little strange, but in a good way.

“Now Cas, if I hurt you-”

“Yeah yeah, I’ll let you know, Dean, just- just go on please,” Castiel said, getting a little impatient. He’d been thinking about this for such a long time and he just needed to feel his lover’s fingers inside of him now.

“Okay, okay,” Dean chuckled a little but then put on his serious face as he focused and brought his two fingers to the older man’s awaiting hole. He made sure to spread the lube around first, rubbing over the pink ring of muscle a few times before he even dared to put pressure.

“Come on, Dean,” Castiel sighed, the anticipation getting the better of him. 

“You know,” Dean said as he bit his lip, “you always tease me like this as well, endless and endless teasing before you do anything to me at all.”

“Dean,” the angel said as he glared at the boy between his legs. He may be on the receiving end this time, but that didn’t mean that Dean could just do as he pleased. 

“Sorry,” Dean blushed at the glare he got from his Dom, he did let himself go a little too much perhaps. But he knew what his place was and always would be Submissive to Castiel. He refocused on the angel’s hole as he slowly pressed his middle finger into the man without too much resistance. 

Castiel didn’t make a sound, he just let out a quick breath and closed his eyes for a moment. Breathe in. Breathe out. One finger was nothing, this was still easy. 

“Good?” Dean asked as he slowly worked his finger in and out of his lover, twisting and turning carefully as he worked him open. 

“Mhm,” Castiel nodded. “One more.”

“Yes Sir,” Dean said but before he pushed a second finger into the angel he moved his free hand to Castiel’s leg, hooking it underneath and placing his hand on the outer side of his thigh. He then pulled out his middle finger, only to have it be joined by his index finger as he pushed the two fingers inside, feeling a little resistance now but he could still slide them in all the way easily.

Dean felt his own cock strain against the fabric of his panties, he took a few deep breaths as he moved his fingers in and out of Castiel, resting his head on the angel’s inner thigh.

“Come on,” Castiel breathed. “One more, Dean.”

The younger man nodded as he pulled his fingers out before adding a third, slowly pushing them back in, this time feeling quite some resistance from his lover.

Castiel closed his eyes and threw his head back, he could really feel Dean’s fingers inside of him now, he wasn’t used to this but it wasn’t an unpleasant feeling. It was quite a comfortable stretch actually.

“May- may I suggest something?” Dean asked carefully, he knew something to help Castiel’s muscles relax, but he wasn’t sure if he was allowed to just… do that without permission. 

“Yes, darling,” the angel nodded as he opened his eyes to look down at his boy, the sight of Dean’s hand working on him making his cock twitch. 

“Some- sometimes when you do… this to me, it erm- it really helps when you suck me off,” Dean blushed a little as he met his Dom’s eyes. “I can try that if you don’t mind?”

“Mhm, you have my permission, but be careful because I don’t know how long I will last with those pretty lips wrapped around my cock,” Castiel said. 

Dean smiled but nodded, shifting a little on his knees so he’d be able to better reach Castiel’s throbbing cock. He had permission to suck his lover off, he wasn’t sure if he had permission for this as well, but he was just going to go for it, he’d probably never get this chance again.

The younger man started by pressing gentle kisses on the inside of the angel’s thigh as he continued to work his fingers in and out of him. He decided to take his time, needing to work Castiel open a little bit more. He had managed to slide his three fingers in all the way now which was good, just a little longer and he could add his pinky as well.

“I’m really proud of you, you know,” Castiel sighed happily as he looked at his boy. “I know this isn’t your usual thing but you’re doing so well.”

“Have an amazing person to look up to,” Dean smiled against the older man’s thigh before moving closer and closer to his cock. He made sure to kiss, nibble and suck on the angel’s pubic area before licking a stripe along his cock. 

“One more Dean, one more and suck me off,” Castiel said, his breaths were getting a little shaky now but he tried to remain his dominant self. 

“Mhm,” Dean agreed and reached for the bottle of lube again, pulling his fingers out of his lover for a moment so he could squeeze more lube onto them. He made sure his entire hand was slick now and even squirted some more on Castiel’s now red hole. 

“Okay,” the younger man said as he pushed his three fingers back in, taking the head of the angel’s cock in his mouth, finally tasting him on his tongue. 

“Fuck Dean,” Castiel groaned, moving his hand to Dean’s hair, gripping onto it tightly.

Dean felt a little proud at the noises he drew from his lover, it wasn’t often that Castiel would let himself come undone like this. He took the angel’s cock a little further into his mouth while at the same time pressing his pinky against his hole. 

“Deep breaths, remember what you always tell me,” Dean said as he pulled off the man’s cock, he had to remind Castiel. 

“Hmm?” Castiel said as he opened his eyes, he was a little too lost to fully understand what Dean had just said. Then he couldn’t help but chuckle.

“What?” Dean frowned.

“Nothing, just think you look absolutely gorgeous with your spit and my cum dripping down your chin,” the angel grinned. “Now, what were you saying?”

“That- that you need to take deep breaths, like you always tell me to,” Dean said as he used the palm of his free hand to wipe his chin clean, then he spat into his hand and brought it to the angel’s cock. “You’ve almost got the pinky too, you’re almost there.”

“Good, yeah, I’ll do that,” Castiel said and as soon as Dean’s head was in reach again his hand was back in Dean’s hair. 

Dean returned to what he was doing and sucked the angel’s cock back into his mouth, his tongue swirling around the head and over the slit as his hand slowly worked up and down the shaft. 

“Oh god Dean,” Castiel moaned and threw his head back. The sensation on his cock was so good that he wasn’t even sure whether he felt something press against his hole or not.

Dean now pushed his pinky in easily, four of his fingers now inside of his lover’s tight hole. He couldn’t help but moan around the cock in his mouth, slowly pulling off with a pop. “You’re almost taking my hand Castiel, almost.”

“It feels- it feels good Dean, so full,” Castiel gasped at the sensation. He wasn’t sure if he could take much more, but he wanted to, god he wanted to.

“I know Cas, but it’ll feel even better,” Dean told his lover. “Are you ready?”

“Mhm, yes Dean, give me your fist,” Castiel breathed heavily, he was so close already. “I’m close Dean, already so close. It want you to come with me baby. Put your pretty mouth back on my cock and use your free hand to stroke yourself.”

“Fuck, yes, yes Sir,” Dean nodded and skillfully pulled his own throbbing cock free from his panties, stroking himself a couple of times before bringing his mouth back to the angel’s cock, taking it deep down his throat like he did best. He had to focus on a lot right now, he wanted to give Castiel the best blowjob he’d ever had while also getting his fist inside AND he had to jerk himself off. 

“Give it to me,” Castiel said as he kept Dean’s head down, his cock fully down the younger man’s throat.

Dean tried to nod, he didn’t care if it looked alright or not. He slowly pulled his four fingers out slightly, folding his thumb against the inside of his hand as he started pushing back in, really feeling the ring of muscle protest against the intrusion, he waited. He waited for a command from his Dom.

“Do it Dean, do it now,” Castiel almost growled, his arousal getting the better of him and he wasn’t sure if he could remain in his dominant role for much longer, he was losing it. 

Dean moaned around the angel’s cock as he pushed, further and further until the ring of muscle passed around the widest part of his hand and his lover’s ass just sucked his hand in, the ring of muscle now tightly wrapped around his wrist.

The most filthy, dirty and extremely loud scream escaped Castiel’s throat as he came down Dean’s throat the second his boy’s fist was inside of him.

Dean swallowed down all the come Castiel had to offer before pulling back from the angel’s cock, he had to see. He had to see how his hand disappeared into his Dom and by god was it a delicious sight. It only took Dean three, four more pumps on his own cock before he too came with a noise they’d never heard from him before.

“You- you did it Cas,” Dean panted heavily as his body was still shocking through his orgasm. He was careful, the angel was wrapped so tightly around his wrist that he was scared to move and hurt the man. 

“Dean that- that was incredible,” Castiel mumbled as he lazily opened his eyes again, watching Dean smile with full, red lips from sucking him off. “Out- out is the worst part isn’t it?”

“I’ll be careful,” Dean said as he casually licked his own come off of his hand. “You push okay?”

“Okay,” Castiel nodded, taking the advice from his boy whom he had fisted so many times before, Dean probably knew best in this situation. As soon as he felt Dean’s hand pulling back he pushed, it was alright until they got to the widest part of Dean’s hand again. “Oh fuck!” Castiel shouted as the widest part of Dean’s hand was removed and the rest followed quickly. His cock twitched pathetically against his stomach, he was spent.

The both of them remained in their positions for a little while, Castiel too wrecked to move as Dean sat on the floor still, admiring his lover’s now slightly gaping and red hole, they actually did it. 

“You did it,” Dean smiled as he leaned in to press a few more kisses against the angel’s thigh.

“No, you did,” Castiel said as he finally let his feet drop from the edge of the couch to the floor, while he did so he felt some lube drip from his ass. “Gotta- gotta clean us up.”

“No,” Dean said as he pushed at Castiel the second he tried to get up. “You just… just stay. I’ll go get us cleaned up.”

“Thank you, Dean,” Castiel smiled and he really meant it, his legs would probably give in the second he got up. 

“More than welcome,” the younger man nodded as he leaned in for a quick kiss before hurrying into the bathroom to get some wipes and towels.

Today was nice, it really was. But next time Dean was definitely going to bottom again.

**Author's Note:**

> Let me know what you think! Also if you would like to read more please let me know!


End file.
